Bufenadrine

Bufenadrine

Clinical data
Other names	B.S. 6534; BS-6534; 2-tert-Butyldiphenhydramine
Drug class	Antiemetic; Antihistamine; Anticholinergic; Antiparkinsonian agent
Identifiers
IUPAC name 2-[(2-tert-butylphenyl)-phenylmethoxy]-N,N-dimethylethanamine
CAS Number	604-74-0
PubChem CID	21916
ChemSpider	20600
UNII	9Y0T619B3U
ChEMBL	ChEMBL2104614
CompTox Dashboard (EPA)	DTXSID70862278
Chemical and physical data
Formula	C21H29NO
Molar mass	311.469 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)C1=CC=CC=C1C(C2=CC=CC=C2)OCCN(C)C
InChI InChI=1S/C21H29NO/c1-21(2,3)19-14-10-9-13-18(19)20(23-16-15-22(4)5)17-11-7-6-8-12-17/h6-14,20H,15-16H2,1-5H3 Key:OGNRRAFRDFGFKA-UHFFFAOYSA-N

Bufenadrine (INNTooltip International Nonproprietary Name; developmental code name B.S. 6534), also known as 2-tert-butyldiphenhydramine, is a drug described as an antiemetic, antihistamine, anticholinergic, and antiparkinsonian agent which was never marketed.^[1][2][3][4] It is the 2-tert-butyl analogue of diphenhydramine.^[2] The drug was found to produce stereoselective hepatotoxicity in animals and this led to the discontinuation of its development.^[2][5] Bufenadrine was first described in the literature by 1967.^[1][4] Its INNTooltip International Nonproprietary Name suffix "-drine" is generally for sympathomimetics but bufenadrine itself is not actually a sympathomimetic or related agent.^[6]

References

1. Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 186. ISBN 978-1-4757-2085-3. Retrieved 17 October 2024.
2. Eichelbaum MF, Testa B, Somogyi A (2012). Stereochemical Aspects of Drug Action and Disposition. Handbook of Experimental Pharmacology. Springer Berlin Heidelberg. p. 422. ISBN 978-3-642-55842-9. Retrieved 17 October 2024.
3. Ariëns EJ (2013). Drug Design: Medicinal Chemistry: A Series of Monographs, Vol. 6. Academic Press. p. 12. ISBN 978-1-4832-1608-9. Retrieved 17 October 2024.
4. Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. William Andrew Publishing. 2013. pp. 704–705. ISBN 978-0-8155-1856-3. Retrieved 17 October 2024.
5. Hespe W, Mulder D, van Eeken CJ (1972). "Differences in metabolic behavior and liver toxicity between the optical isomers of bufenadrine hydrochloride, a substituted diphenhydramine, in the rat". Acta Pharmacol Toxicol (Copenh). 31 (5): 369–379. doi:10.1111/j.1600-0773.1972.tb03600.x. PMID 4678820.
6. "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.